Journal of Organic Chemistry p. 5214 - 5217 (1984)
Update date:2022-08-24
Topics:
Casal, H. L.
Werstiuk, N. H.
Scaiano, J. C.
Diphenylcarbene reacts with 2,2,6,6-tetramethylpiperidine N-oxide with a rate constant of 2.7 x 108 M-1 s-1 in acetonitrile at room temperature.The reaction involves the thransfer of an oxygen atom, leading to benzophenone and 2,2,6,6-tetramethylpiperidinyl radical in essentially quantitative yields.In the case of 4-hydroxy-2,2,6,6-tetramethylpiperidine N-oxide insertion at the O-H bond competes with reaction at the nitroxide center, with rate constants of 1.9 x 107 and 2.8 x 108 M-1 s-1, respectively.The reaction of the OH site is not enhanced significantly by the presence of a paramagnetic center in the molecule.
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